ES2050069A1 - Prepn of anti-psychotic pyrimidinone - which is 3-(2-(4-(6-fluoro- 1,2-benzisoxazol 3-yl)piperidino) ethyl)-2-methyl- 6,7,8,9-tetra- hydro-4H-pyrido (1,2-a) pyrimidin-4-one - Google Patents
Prepn of anti-psychotic pyrimidinone - which is 3-(2-(4-(6-fluoro- 1,2-benzisoxazol 3-yl)piperidino) ethyl)-2-methyl- 6,7,8,9-tetra- hydro-4H-pyrido (1,2-a) pyrimidin-4-oneInfo
- Publication number
- ES2050069A1 ES2050069A1 ES9201424A ES9201424A ES2050069A1 ES 2050069 A1 ES2050069 A1 ES 2050069A1 ES 9201424 A ES9201424 A ES 9201424A ES 9201424 A ES9201424 A ES 9201424A ES 2050069 A1 ES2050069 A1 ES 2050069A1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- pyrido
- pyrimidin
- ethyl
- benzisoxazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 title abstract 2
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 title 1
- 230000000561 anti-psychotic effect Effects 0.000 title 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- WQJPGQDCLBMXMH-UHFFFAOYSA-N (2,4-difluorophenyl)-piperidin-4-ylmethanone Chemical compound FC1=CC(F)=CC=C1C(=O)C1CCNCC1 WQJPGQDCLBMXMH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Prepn. of 3-(2-(4-(6-fluoro-1,2 -benzisoxazol-3-yl) piperidino)ethyl) -2-methyl-6,7,8,9- tetrahydro-4h-pyrido -(1,2-a) pyrimidin-4-one. (I) comprises reacting a cpd. of formula ZCH2CH2L with 4-(2,4-difluoro benzoyl)piperidine to give 3-(2-(4-(2,4- difluorobenzoyl) piperidin)-ethyl) -2-methyl-6,7,8,9- tetrahydro-4H-pyrido (1,2-a) pyrimidin-4-one, which is reacted with hydroxylamine hydrochloride to give the corresp. oxime 3-(2-(4-(1-(2,4- difluorophenyl)-1- (hydroximino)methyl) piperidin)ethyl) -2-methyl-6,7,8,9- tetrahydro-4H-pyrido (1,2-a)pyrimidin-4-one which is cyclised under basic conditions to give (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9201424A ES2050069B1 (en) | 1992-07-10 | 1992-07-10 | PROCEDURE FOR OBTAINING 3- (2- (4- (6-FLUORO-1,2-BENZISOXAZOL-3-IL) PIPERIDINO) ETIL) -2-METHYL-6,7,8,9-TETRAHIDRO-4H-PIRIDO (1,2-A) PIRIMIDIN-4-ONA. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9201424A ES2050069B1 (en) | 1992-07-10 | 1992-07-10 | PROCEDURE FOR OBTAINING 3- (2- (4- (6-FLUORO-1,2-BENZISOXAZOL-3-IL) PIPERIDINO) ETIL) -2-METHYL-6,7,8,9-TETRAHIDRO-4H-PIRIDO (1,2-A) PIRIMIDIN-4-ONA. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2050069A1 true ES2050069A1 (en) | 1994-05-01 |
| ES2050069B1 ES2050069B1 (en) | 1994-12-16 |
Family
ID=8277596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9201424A Expired - Lifetime ES2050069B1 (en) | 1992-07-10 | 1992-07-10 | PROCEDURE FOR OBTAINING 3- (2- (4- (6-FLUORO-1,2-BENZISOXAZOL-3-IL) PIPERIDINO) ETIL) -2-METHYL-6,7,8,9-TETRAHIDRO-4H-PIRIDO (1,2-A) PIRIMIDIN-4-ONA. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2050069B1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001085731A1 (en) * | 2000-05-05 | 2001-11-15 | Rpg Life Sciences Limited | A PROCESS FOR THE PREPARATION OF ANTI-PSCHOTIC 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2,-a]pyrimidin-4-one |
| WO2004009591A1 (en) * | 2002-07-22 | 2004-01-29 | Aurobindo Pharma Ltd. | A process for the preparation of antipsychotic risperidone |
| WO2004035573A1 (en) * | 2002-10-18 | 2004-04-29 | Hanmi Pharm. Co., Ltd. | Method for preparing risperidone |
| WO2004020439A3 (en) * | 2002-08-30 | 2004-07-01 | Sunil Sadanand Nadkarni | Improved process for preparation of risperidone |
| WO2006005974A1 (en) * | 2004-07-08 | 2006-01-19 | Richter Gedeon Vegyészeti Gyár Rt. | A process for the preparation of risperidone |
| WO2006046082A1 (en) * | 2004-10-25 | 2006-05-04 | Richter Gedeon Vegyészeti Gyár Rt. | A process for the preparation of risperidone |
| US7256195B2 (en) | 2000-08-14 | 2007-08-14 | Teva Pharmaceutical Industries Ltd. | Preparation of risperidone |
| CN100390146C (en) * | 2002-11-13 | 2008-05-28 | 斯索恩有限公司 | Process for preparing risperidone and intermediates therefor |
| CN115057809A (en) * | 2022-07-15 | 2022-09-16 | 扬州市普林斯医药科技有限公司 | Preparation method of 4- (2, 4-difluorobenzoyl) -piperidine |
| CN117700411A (en) * | 2023-06-05 | 2024-03-15 | 山东康诺生物工程有限公司 | A synthesis method of key intermediates of paliperidone |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050232995A1 (en) | 2002-07-29 | 2005-10-20 | Yam Nyomi V | Methods and dosage forms for controlled delivery of paliperidone and risperidone |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110435A1 (en) * | 1982-11-01 | 1984-06-13 | Janssen Pharmaceutica N.V. | Novel ((bis(aryl)methylene)-1-piperidinyl)alkyl-pyrimidinones |
| ES8705881A1 (en) * | 1985-03-27 | 1987-05-16 | Janssen Pharmaceutica Nv | New 3-piperidinyl -1,2-benz-isothiazole and -isoxazole derivs. |
| EP0368388A2 (en) * | 1988-11-07 | 1990-05-16 | Janssen Pharmaceutica N.V. | 3-Piperidinyl-1,2-benzisoxazoles |
| EP0453042A1 (en) * | 1990-04-19 | 1991-10-23 | Janssen Pharmaceutica N.V. | Novel 2,9-disubstituted-4H-pyrido-[1,2-a]pyrimidin-4-ones |
-
1992
- 1992-07-10 ES ES9201424A patent/ES2050069B1/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110435A1 (en) * | 1982-11-01 | 1984-06-13 | Janssen Pharmaceutica N.V. | Novel ((bis(aryl)methylene)-1-piperidinyl)alkyl-pyrimidinones |
| ES8705881A1 (en) * | 1985-03-27 | 1987-05-16 | Janssen Pharmaceutica Nv | New 3-piperidinyl -1,2-benz-isothiazole and -isoxazole derivs. |
| EP0368388A2 (en) * | 1988-11-07 | 1990-05-16 | Janssen Pharmaceutica N.V. | 3-Piperidinyl-1,2-benzisoxazoles |
| EP0453042A1 (en) * | 1990-04-19 | 1991-10-23 | Janssen Pharmaceutica N.V. | Novel 2,9-disubstituted-4H-pyrido-[1,2-a]pyrimidin-4-ones |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001085731A1 (en) * | 2000-05-05 | 2001-11-15 | Rpg Life Sciences Limited | A PROCESS FOR THE PREPARATION OF ANTI-PSCHOTIC 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2,-a]pyrimidin-4-one |
| US7256195B2 (en) | 2000-08-14 | 2007-08-14 | Teva Pharmaceutical Industries Ltd. | Preparation of risperidone |
| WO2004009591A1 (en) * | 2002-07-22 | 2004-01-29 | Aurobindo Pharma Ltd. | A process for the preparation of antipsychotic risperidone |
| WO2004020439A3 (en) * | 2002-08-30 | 2004-07-01 | Sunil Sadanand Nadkarni | Improved process for preparation of risperidone |
| US7202360B2 (en) | 2002-10-18 | 2007-04-10 | Hanmi Pharm Co., Ltd. | Method for preparing risperidone |
| WO2004035573A1 (en) * | 2002-10-18 | 2004-04-29 | Hanmi Pharm. Co., Ltd. | Method for preparing risperidone |
| CN100390146C (en) * | 2002-11-13 | 2008-05-28 | 斯索恩有限公司 | Process for preparing risperidone and intermediates therefor |
| US7405298B2 (en) | 2002-11-13 | 2008-07-29 | Synthon Ip Inc. | Process for making risperidone and intermediates therefor |
| WO2006005974A1 (en) * | 2004-07-08 | 2006-01-19 | Richter Gedeon Vegyészeti Gyár Rt. | A process for the preparation of risperidone |
| EA011748B1 (en) * | 2004-07-08 | 2009-06-30 | Рихтер Гедеон Ведьесети Дьяр Рт. | A process for the preparation of risperidone |
| WO2006046082A1 (en) * | 2004-10-25 | 2006-05-04 | Richter Gedeon Vegyészeti Gyár Rt. | A process for the preparation of risperidone |
| CN115057809A (en) * | 2022-07-15 | 2022-09-16 | 扬州市普林斯医药科技有限公司 | Preparation method of 4- (2, 4-difluorobenzoyl) -piperidine |
| CN115057809B (en) * | 2022-07-15 | 2024-02-13 | 扬州市普林斯医药科技有限公司 | Preparation method of 4- (2, 4-difluorobenzoyl) -piperidine |
| CN117700411A (en) * | 2023-06-05 | 2024-03-15 | 山东康诺生物工程有限公司 | A synthesis method of key intermediates of paliperidone |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2050069B1 (en) | 1994-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA2A | Application withdrawn |
Effective date: 19950425 |